


Keeping Daddy Company at Work

by Taybay14



Series: Adventure's of Sam & His Little Catboy Gabe [1]
Category: Supernatural
Genre: (but not really shota, Alpha/Beta/Omega Dynamics, Anal Sex, Butt Plugs, Butt Slapping, Catboy Gabriel (Supernatural), Catboys & Catgirls, Cock Slut, Cock Warming, Come Inflation, Consensual, Daddy Dom Sam Winchester, Daddy Kink, Dirty Talk, Fluff, Fucking Machines, Gabe in panties, Gabe is of age, Gabriel likes many things from little space/is very little in his head, M/M, Mating Cycles/In Heat, Needy Gabriel (Supernatural), Non-Traditional Alpha/Beta/Omega Dynamics, Owner Sam, Pacifiers, Plot What Plot/Porn Without Plot, Praise Kink, Sex Toys, Shameless Smut, Shota Gabriel, Size Kink, Smut, Spankings, Stuffies, catboys/girls age much differently so he is OF AGE), he's just a cute little cat boy who loves being spoiled and being little, minor speech impediment for Gabe, once again, pacis
Language: English
Status: Completed
Published: 2019-03-03
Updated: 2019-03-27
Packaged: 2019-11-08 08:46:35
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 5,730
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17978114
Author URL: https://archiveofourown.org/users/Taybay14/pseuds/Taybay14
Summary: I received a prompt from anon : I would honestly lose my mind over a fic that shoes more of the Sabriel side of "Dean's Special Little Catboy." It would be really amazing if they got their own spin-off fic, but I would settle for a one-shot that shows more of their relationship. Smut would be nice, but even just a glimpse of their day to day life would be great.For now, at least, this will just be a collection of one shots about Sam & Gabe, taking place before and during "Dean's Special Little Catboy"-- if you like this, check out my multi-chapter porn with plot "Dean's Special Little Catboy" !!!!





	1. Chapter 1

Sam Winchester has never felt so relieved for a work meeting to be over. It was a long, dry, pointless one. The kind where Sam just wants to scream at his clients to get their shit together. That's not what lawyers do, though, so instead he has to sit back and suffer in silence.

He's just thankful he finally got to start his own law office. He sets his own hours, picks his own staff, and decides what cases he wants. It even gives him time for pro bono cases. 

Best of all? No one can give him shit for having his catboy at work. 

When he enters his private office inside the firm, he finds his boy on the burgundy rug in front of the fireplace. He's laying on his belly with his little feet swaying in the air as he colors in the new Princess book Sam bought him this past week. A plate of carrot sticks, cheese, and crackers is beside him with his sippy cup full of juice. 

Sam doesn't even close the door before he sees Gabriel's little cat ears perk. He hears a distant sniffing sound and then the catboy is up and running to him.

“Daaadddy!” He launches into Sam's arms, wrapping his skinny legs around his waist and wiry arms around his neck, squeezing. “I missed you soooooo much. You was gone fowevew!” 

“I know. Daddy missed you too.”

He wiggles in excitement. “We go home now?”

“Daddy has a little more work to do. But if you're a really good boy, we can go to the park after.”

Gabriel's eyebrows raise. “And ice cweam?” 

Sam laughs and plants a kiss on Gabriel's nose, making the kitten squirm and giggle. “Ice cream too.” 

“Yaaaay!” He claps his hands and wiggles, a silent request for daddy to put him down. 

When Sam puts him on his feet, he settles on his belly again and returns to coloring. It's a picture of Minnie Mouse holding a heart. He wants to write ‘I love you daddy’ but his little mind is hurting from trying to remember his lessons. His pink tongue sticks out of the corner of his mouth as he concentrates. It takes time but then he's finished. 

He hops up and runs over to his daddy, tugging on his shirt sleeve to get his attention. Sam looks down to see his little one proudly holding the piece of paper colored in chaotic scribbles with I Luv U Dady in choppy handwriting. 

Sam's heart skips. “Oh baby. I love it so much! Thank you.”

Gabriel puffs up with pride, cheeks turning pink. He fiddles with his pretty yellow dress, tiny fingers loving the feel of the tutu material against them. He loves being dressed in pretty things but he loves being nakey more. He wishes they were home already so he could strip down. He could take a nice warm bubble bath, and then daddy would lotion him up and make him smell all nice. Then he could snuggle nakey on daddy’s lap, feeling daddy’s big hands stroking his soft skin. Maybe keep his cock warm for a while. They could watch a movie.

He sighs. “Daddy, you done yets?”

“No, baby. I need maybe one more hour.”

“Bit I bowed.”

“Hi bored, I’m daddy.” 

Gabriel frowns at his daddy, eyebrows pulling in. His daddy is always making terrible daddy jokes, and they usually get him to smile, but not today. He’s putting his tiny foot down. If he giggles and forgives him, he’ll be bored for another hour. If he continues to be angry and pouty, maybe daddy will decide to leave early. Or at least figure out a way to entertain him in the meantime. 

Sure enough, his daddy looks sad and guilty. He reaches out and takes the kitten into his arms. Gabriel straddles his lap and places his two small hands on his daddy’s chest, kneading him. 

“Do you want to keep daddy company while he writes his brief?”

Gabriel tilts his head at that last word. He’s heard it before. “Bwief means fast and showt. Dat dis?”

Sam smiles. “In a way. It’s fast and short compared to what the information actually is, but it’s not fast and short like it will be done quick. It’s gonna take me about an hour or so, bud.”

His bottom lip curls out, wet and plump, trembling with sadness. Sam can never resist that bottom lip. It gets Gabriel everything. 

“Oh, baby boy.” He cradles the back of Gabriel’s head and guides that pouty lip to his mouth. The kitten shivers, then moans when his daddy licks along the seam of his lips. He opens and tilts his head. Sam takes advantage of the new position and begins to devour him. It’s been a few hours since he kissed his boy last. He had tasted like mint toothpaste and candy. Now, he tastes like his apple juice. Sam licks inside his mouth, tangling their tongue together, groaning at the rough texture of his kitten’s tongue against his. 

He unzips his pants and fiddles with it to release his hard and aching cock. Gabriel gets up on his knees to give him more room to work, the kiss continuing. He’s not wearing any panties so all Sam has to do is pull out his sparkly pink plug. It’s a small one and his baby could probably use some prep, but Sam is too desperate. He breaks their kiss, latching his mouth onto the spot on Gabriel’s neck that drives the boy absolutely wild. He bites down hard, then sucks away the pain. When he feels a rush of slick covering his hand and dick, he uses it to lube up and slams into his kitten. 

The noise Gabriel makes is loud and sharp, somewhere between a desperate keen and a cry for help. Sam doesn’t give him time to adjust. Gabriel wouldn’t want him to, anyway. The little one likes things on the rougher side most times. He likes to feel how big and strong his daddy is. 

Tears streak down his face as his daddy fucks up into him. He huffs and pouts under his breath, sniffling and hiccuping. It doesn’t take long for his well-used hole to remember how to take his daddy, though. Then it’s fluttering open beautifully. Swallowing Sam whole. Taking him deep enough to make Gabriel feel him in his tummy. It took Sam seven months to be able to bury himself completely in Gabriel. It had been a frustrating process. Everyone thinks having a monster dick is great, but not when all you want to do is fuck the shit out of your tiny kitten and can’t. 

The training was sure as hell fun, though. 

And now, Gabriel takes him like a champ. Fucking loves his daddy’s monster cock. Loves the feel of being split open and stuffed full. 

“Daddy, daddy,” the kitten whispers, riding him in frustration. Sam has stopped moving now. He’s grinning at his boy. It’s a teasing smile that Gabriel doesn’t think he likes much. “Daddy, move.”

“No. You’re here to keep me warm.”

The kitten looks up at him, sad brown eyes watery and red rimmed. “But - but- but we-”

“Hush.” Sam takes the back of his head and guides him forward until his face is in his neck. Gabriel sniffles and wraps his arms around his daddy’s neck, smearing his tears against the skin there. He feels a kiss pressed to his temple, eyes fluttering shut despite his anger. It’s really not that bad. Sure, daddy got him super horny, but daddy had to get him like that for his big cock to fit inside him. At least he gets to warm daddy’s cock now. Maybe he can even take a little kitten nap. Then daddy will fuck him for real, fill him up, plug him, and they can go to the park and eat ice cream. 

Sighing in happiness with this new plan of action, Gabriel wiggles a little to get his daddy’s cock in a more comfortable spot, then relaxes into him and lets himself drift into a blissful rest. 

 

\----

 

Gabriel wakes up to pure pleasure and the feeling of being full, full, full. He blinks open his sleepy eyes, looking down at his little kitty cock pressed against his daddy’s tummy. It’s drooling on daddy’s nice work shirt. He doesn’t know when daddy took his dress off but he’s not complaining. He just leans forward so his sensitive rose bud nipples get to feel the nice scritch scratch of his daddy’s shirt. When the sensation sends a zing up his spine, he shivers and moans. 

“Oh, daddy.”

“What baby?”

“Feews soooooooo good.”

Sam grins down at him, loving the way his boy looks when he’s out of his mind with pleasure. The bright eyes full of tears. The bright pink cheeks. The constant twitching of his kitten ears. The way his pouty little mouth drops open in a perfect, pink ‘o’ that Sam just wants to fuck with his cock. 

Leaning forward, he latches his mouth around one of those perfect perky nipples and sucks at it, harsh and fast. The kitten rocks on his cock, mewling. His claws dig into Sam’s chest but he doesn’t care. He just grunts through the pain and continues to fuck up into him. 

His poor boy pussy flutters and retracts around daddy’s huge cock as he gets closer and closer to that explosion daddy always gives his belly. Sam can feel the shift and stands up, keeping Gabriel firmly on his cock. He lays the boy on his desk and leans over so he’s fucking into him hard. His little feet rest on Sam’s shoulders, the angle making him go impossibly deep and hit just the right spot every time he thrusts in. 

With his next thrust, Gabriel yowls and shoots a load onto his little belly. One of his hands grabs his cocklet and starts rubbing at it like it wasn’t enough. “Needs you daddy. Need daddy’s commies in my bewwy.”

“I know, baby. Be patient.”

The little one whimpers and nods, his powdery pink prick already watering again from the rough abuse of his tiny hand against it. Sam traces the outline of his cock moving in his boy's belly. He shivers as he feels himself through the kitten's silky skin.

His kitten starts crying again, tugging at his kitty cock too hard in desperation. Sam moves his hand away to keep him from hurting himself and spits a glob down onto the boys smooth cock and hairless little balls. He uses it as lube and starts working his baby boy into his second orgasm. 

“Come for daddy and I'll give you my commies.”

“Oooooh, yes daddy! Pwease!” He twitches his thin hips and gasps, cheeks and tips of his human ears turning pink, tail coming around to brush against his little cock that's being rolled between his daddy's two fingers. The feel of the hair tickling him is enough and he shoots watery little spurts of kitten come onto himself. Sam lets go of his cocklet and grabs his hips hard enough to bruise, slamming into him three times roughly before stilling and filling him. 

Even after he pulls out, there's a tiny bulge in his kitten's soft tummy from where he dumped his load. He plugs his hole, then scoops him up to carry him to the adjoining bathroom. After he cleans and dresses his boy again, the sleepy kitten looks up at him, rubbing at an eye. 

“We go pawk now? ‘N ice cweam?” 

Sam laughs, ruffling his boys pretty blonde curls. “Of course, buddy. Let's go.”


	2. Chapter 2

**Summary for the Chapter:**

> Gabriel gets in trouble at the park

The park is fairly busy, which isn't surprising with it being such a beautiful day out. Sam had stopped home quick to change into shorts and a shirt, and to let Gabriel grab his favorite toy airplane. When they drive up to the park, Gabriel goes crazy from impatience. The catboy wriggles and pouts at being locked in, making grabby hands at all the kids running free. 

“Calm down. Calm down.” Sam laughs, unbuckling himself and opening the car door. Once freed, the kitten clambers out and runs away, straight for his favorite part of the park - the swings. 

Sam follows, picking him up and placing him on one of the swings since he's too short to hop up on it without falling. His tiny hands cling to the chains as Sam slowly starts to push him. He tries to kick his legs and pump like his daddy taught him but just ends up making the swing twist in a scary way that he doesn't like one bit.

Huffing in frustration, he hops off the swing and goes running again. When he picks the giant jungle gym, Sam sits on a bench that has a clear view of every part. He leans back and soaks up the sun as he watches Gabriel. He's a total social butterfly, and is rarely shy. He wishes the boy had more friends. With it being summer, school is out, and Sam doesn't have any friends with catboys or girls. His friend Balthazar has a dogboy, but that makes him too nervous. He's heard horror stories of dog boys pinning catboys and girls down and knotting them. 

At least all catboys and girls are genetically created to be omegas, so if they do get out of hand at a playdate, no baby kittens come out of it.

Sam has been trying to convince his brother to get a catboy, but Dean always just waves him off. He claims he'd be shit at taking care of one but Sam knows it's a lie. Dean is a fantastic uncle to Gabriel. The kitten loves his special sleepovers there. 

Gabriel comes out of the tunnel he was in, holding the hand of a little catboy dressed in frilly lace shorts that show the curves of his buttcheeks and a tank top that shows his midriff. Sam's eyes narrow as he watches the two carefully. He's explained to Gabriel the rules with other catboys and catgirls, and human kids, and he knows he can't have any special friends. He's Sam's. Only Sam's. 

But, at his age, holding hands is harmless. Gabriel’s done it before with friends from school or playmates at places like the park or library. 

Still, Sam tracks their every move. 

\-----

Gabriel and his new friend, Kevin, sit down on the edge of the Merry-go-round. The metal is warm against their bare thighs and it feels nice. Kevin’s playing with the fluffy yellow tutu part of Gabriel’s pretty dress. It tickles as he moves it against Gabriel’s skin.

“Dis is vewy beautifuww,” Kevin tells him eventually. 

“Tank you.” Gabriel reaches a tiny hand over, running his fingers along the delicate lace of the other boy’s shorts. “Dis vewy beautifuww too.” 

“Tanks.” Kevin wiggles his butt, blushing under the praise. “Does you have a mommy ow a daddy, ow a masta?” 

Gabriel looks around for Sam, smiling and waving at him when he sees his daddy watching. Then he points a finger for Kevin and says, “Daddy. He ovew dewe. His names Sam.”

“Oh, he vewy handsome.”

“He is.” Gabriel takes Kevin’s hand in his again, missing the contact. “Wha’s ‘bout you?”

“I has a daddy, too!” He points over to the opposite side of the park, where a man with dark black hair is holding a catboy that’s curled up in a ball in his lap, holding tight to a teddy bear and sucking on a pacifier. “Dats my new baby bwodew. He sad aaaawwwwwwwwl da time.”

Gabriel makes a face, understanding how annoying that would be. Still, having a brother sounds like lots of fun. He’s always wanted a brother, or even a cousin. He sometimes overhears his daddy try to get his Uncle Dean to buy a catboy and he always crosses his fingers, squeezes his eyes tight, and makes a really big wish that he will. That’d be even better than a brother, because when the catboy gets really annoying or cries too much, then Gabriel and his daddy can just leave and get alone time. It’s a perfect plan. 

Tilting his head at the little boy in Kevin’s daddy’s lap, Gabriel examines him. “Is he nice?”

“Umms,” Kevin sighs dramatically. “He is. Daddy says we gotta give him time to adjus’, so I twyin’ to be patient.”

“Dat mus’ be hawd.”

“Yeah. Daddy no fuck my howe in two whole weeks!” 

“What!?” Gabriel snaps his head to look at him in shock, pink mouth dropping. “Has you gotten miwk?”

The little catboy shakes his head sadly, pouting. Gabriel hurries to throw his wiry arms around Kevin’s tiny frame, squeezing him tight. The other catboy winds around him and starts to purr. The noise makes Gabriel’s little cocklet start to harden and leak. Kevin smells it and whines, wiggling his hips as his own does the same. 

“Gabe?” Kevin asks quietly in his ear. “Wiww you pway wiff my cock and boy pussy?” 

Gabriel gasps in surprise, pulling back to look at him. He can’t help but feel a rush of slick at the thought. He’s never fucked anyone before, but his daddy does it really good, and he thinks he could at least try to recreate that. 

Daddy said he’s not allowed to kiss other boys or girls, though. And they aren’t allowed to touch his little kitty parts. 

But what daddy doesn’t know doesn’t hurt him. He heard his daddy say something like that once, when he was at work. 

Taking Kevin’s little hand, he looks at the boy very seriously and whispers, “Wets go hide in da tunnew ‘n I gives you spessal kitty kisses there.”

Kevin nods frantically. They squeeze hands and sprint over to the tunnel, already panting before they’re even out of breath from the exercise. They clamber up the ladder and crawl into the big pink tube that doesn’t have any holes or cutouts for their daddies to see them. 

“Now what?” Kevin asks with wide eyes, unsure of the following steps. This is when daddy gives him an order. 

Gabriel is just as lost. He wiggles a little in anxiety. “Umms, well, takes your showts off fiwst. ‘N panties.” 

“Yes! Good. Oskay.” Kevin shimmies the lace shorts and silky pink panties down his thighs and to his ankles. His cocklet is bright red and leaking, and slick coats the inside of his thighs and down his legs. It’s been so so long since anyone has touched him. He knows Gabriel won’t be as good as his daddy, but it will at least be something more than what he’s been doing, which is pathetically fucking himself on his tail or tiny fingers he can’t get fully inside because of the awkward angle. 

Licking his lips, Gabriel crawls over to him and takes his pretty kitty cock into his mouth, swallowing him down. When he gets to the bottom, he sticks out his tongue to lap at the catboy’s small ball sack. 

“Oh! Oh!” Kevin thrusts up into him, but this isn’t what he wants. This isn’t good enough. “My howe, Gabe. Pwease. Pwease. My howe.”

With a loud pop, Gabriel pulls off of Kevin’s boy parts to focus on his boy pussy instead. He pushes him onto his back and gets an idea. He’s seen it only in the catboy dirty videos daddy has him watch sometimes when he’s in heat and hooked up to the fucking machine. He straddles Kevin so that his face is near his cock and pussy, while his own boy pussy is right in front of Kevin. 

Gabriel spreads Kevin’s legs and pulls them back so he has better access to the tight, needy, neglected hole. He licks down his cock, the seam of his balls, past that super sensitive piece that daddy always presses, and to his hole. He swirls around, lapping at all the slick, smiling at the taste of strawberry. 

“Oh, yes. Yes!” Kevin pants as Gabriel starts to eat out his hole. He wants to share the pleasure, so he pushes Gabriel’s pretty dress back and removes his plug. All of his daddy’s come from earlier starts gushing out and Kevin groans at the smell of a daddy’s milk, even if it isn’t his own. Before any can go to waste, Kevin starts licking it all up. When there’s no more left to clean up, he pouts and puts his mouth over the fluttering little pink hole, sucking and slurping all the milk he can get, making sure to fuck his tongue into him and swirl it around for any leftovers. 

At the same time, Gabriel is working his third finger into Kevin’s hole, fucking him and trying to find that special spot he loves when his daddy touches. 

Then all stimulation is gone, and big, strong hands are yanking Gabriel out of the tunnel. He’s still a little dazed from pleasure so it takes him a moment to register that his daddy has him. 

Sam glares down at his catboy, with his bright pink cheeks, flattened kitten ears, and pouty lip. He immediately starts chanting, “Sowwy! Sowwy, daddy! Sowwy!”

“Hush,” Sam growls, swatting him on his naked little butt in front of everyone. 

Crying, Gabriel tries harder to get his daddy to understand. “He wonewy! He no gets miwk fwom his daddy! I jus’ twyin’ to hewp him. He was so sad! Aww awone and wonewy. I twyin’ be good fwiend!” 

“That’s enough!” Sam barks. His yelling mixes with the yelling of the other dad, who is holding a squirming catboy in his arms while another one hangs off his back, sucking on a pacifier. 

The two dads make eye contact and Sam shakes his head. “I am so sorry. I don’t know what got into him. He knows better than this.”

The other dad, who looks utterly exhausted, assures him, “It’s Kevin. He’s been acting up. I’m sorry he got your boy involved.”

“Daddy!” Kevin screeches, getting impatient and frustrated because he’s trying to explain to his daddy that he’s not being naughty, he’s just tired of being ignored and lonely. He gets a swat on his butt like Gabriel, but at least his daddy whispers afterwards that he promises they can talk about it when they get home. 

When Sam gets Gabriel to the car, he has his arms full of a sobbing catboy. He’s pleading frantically and kicking his skinny little legs out. “Daddy! Daddy, no! Pwease! Wisten, daddy, wisten!”

“You keep yelling and throwing this tantrum, and your punishment is going to get even worse. And, trust me, it’s already really bad, Gabe. So behave.”

The kitten buries his face in his tiny hands and cries into them, shaking violently as his daddy straps him into his carseat. He hates his carseat, and his daddy knows it. Usually he’s allowed to sit in Daddy’s lap, either watching out the window or sitting with his belly against his daddy’s belly, arms wrapped around his neck so he can cuddle him while they drive. 

Then he realizes something even worse once he’s strapped in. “Wait! Daddy! We no gets ice cweam yets!”

“You think you’re getting ice cream after that?” Sam asks incredulously. “Little boy, you’re lucky if I feed you dinner. Now be quiet and think about what you did and how sorry you are.”

Gabriel slumps in his seat, tiny legs dangling, toes wiggling because he has grass and dirt in them and it’s bothering him. He wants to ask daddy to give him a bubble bath and make him nice and clean, but he knows that won’t be happening. 

Daddy is going to punish him. Gabriel hates hates hates punishments. His daddy is rough with him, and sometimes his daddy doesn’t even fuck him or give him milk after! He’ll just hurt him and make him super sad, and then make him go to sleep! 

His little butt is already aching just imagining what his daddy will do to it.


	3. Chapter 3

**Summary for the Chapter:**

> Gabriel gets his punishment  
> \- I want to reiterate that Gabe is a mild masochist & likes things on the rougher side, so his punishments can get pretty rough. He DOES have a safeword, as well as a non-verbal safeword, so don't worry.

“Such a slutty, naughty little boy,” Sam chastises as he carries Gabriel into their playroom at the house. 

Gabriel knows better than to argue or cry but he can’t help it. It’s self preservation. “Please, daddy! I so sowwy! I sowwy! Pwease!”

Rolling his eyes, Sam places him on the nearest surface and yanks his clothes off him, not caring when the kitten starts to sob from his pretty dress being ripped. He grabs his boy’s hot pink ball gag and shoves it between his petal soft lips, securing it so he’s stuck in a natural ‘O’ of surprise. 

“Now, hush. I’m sick of it. I’m sick of that lying, sassy little mouth of yours. In fact, I think I should keep you gagged forever.” 

Now that he doesn’t have to listen to his little boy’s whining, Sam grabs the naked kitten with harsh hands and throws him over the spanking bench. He doesn’t have to secure Gabriel’s hands or feet; he knows he won’t fight or run. He’ll just sob and pant. 

Sam brings down a hand on the sweet little bottom two times, hard and fast, grinning as his handprint appears in a beautiful cherry red. He picks up his pace and continues onward until the skin of the boy’s ass cheeks and lower thighs are the same color. When he’s done, his little one’s tiny fists are balled up and he’s lying in a puddle of snot, tears, and drool. 

Leaving him in place, Sam reaches up and unclasps his gag, leaving Gabriel’s mouth free. The boy doesn’t speak or make any noises other than loud, desperate, choked sobs. 

“You want to act like a little slut? How about you show me what a little slut you can be.” Sam grabs him and brings him to the large bed in the center of the playroom. He puts him on his back and goes digging in one of the drawers nearby. He takes out one of the miniature cock rings made specifically for tiny catboys like Gabriel. He secures it around the boy’s sad, weeping little cocklet and grins when it makes his kitten sob harder. 

Standing back and crossing his arms over his chest, Sam orders, “Fuck yourself with your tail, you little slut.”

“Daddy! Daddy, pweaaaseee,” he sobs, shaking his head even as he pokes the tip of his tail at his soaking wet hole. The pucker flutters open as it’s tickled by the fur and he moans without meaning to, his gangly little legs spreading further open. 

“You know what? I don’t enjoy this view enough. Get on your hands and knees so I can see you fuck yourself like a slut.”

“Y- y- yes daddy.” The boy hurries to roll over and scrambles into the correct position. His knobbly knees are shaking so hard they can barely keep him up but he makes do. The new angle opens his hole wider and the tail slips in further. Nice and deep. It rubs against his prostate and he throws his head back in a pained yowl. 

Sam just chuckles and walks over to the dresser, getting bored of the tail. He needs to see his boy gaping open and desperate. 

He grabs a large dildo and climbs onto the bed. Holding it firmly with his hands, he rests it in the air a few inches from Gabriel’s slutty hole and orders, “Keep the tail in. Fuck yourself back on this big cock.”

“Daddy!” the little kit squeaks, looking back at him with wide and watery eyes. “No!”

Sam reaches out and smacks a hand down hard enough to cut a part of his boy’s skin where the heel of his hand hits the curve of his ass cheek. “Shut up! Fuck yourself!”

The boy sobs and crumbles, but he pushes back on his little hands and knees and forces his hole to start sucking in the dildo alongside the scratchy tail inside him. As the dildo presses into him, the tail is shoved into that sensitive spot inside of him. It’s damn near torture. 

Once the kitten is seated fully on the dildo, Sam shoves him to his stomach on the bed and grabs his hips to lift them up in the air. He uses his grip on the edge of the dildo to fuck it into his hole hard and fast, just laughing as the kitten kicks and shrieks. The boy has a safe word but he won’t be using it. Sam knows his slutty little kitten. His slut likes it like this. He gets off on pain and humiliation. Sam could walk him around a bar tonight with the word SLUT markered on him and the boy would blush and sob but he’d come beautifully, all over himself, unbelievably horny from the embarrassment. 

After he’s nearly crazy with need, the kitten finally breaks and starts to speak out of turn again, not caring that it will mean punishment. “Pwease! Oh, daddy, pwease! Pwease wet me comes. Wet me comes. Pwease.”

“Fine.” Sam takes the cockring off and lets his boy shoot a load right on the spot. Then he wraps two big fingers around the kitty’s cocklet to continue jacking him off, just smirking when the boy chokes on the pain from being oversensitive. 

“Pwease! Stop! Oh, stop! Stop!” The boy writhes and kicks and shrieks, snot and tears all over his body now. His tiny cock keeps shooting load after load and he’s choking on air. 

Finally - finally- Sam gives him a break by stepping away. The kitten pants and heaves with his face smashed into the mattress. He trembles and squeezes the sheets in his tiny hands. Sam pulls out the fucking machine, the one with the restraints, and pulls it to the edge of the bed. He secures him to the machine with the leather straps, nice and tight, letting them dig into his skin. The boy starts to pant and beg again. Beg him to stop. Beg him to not do this. 

“Since you’re too much of a slut, I’ll hook you up to this machine and watch you get fucked hard for as long as I see fit. Maybe by the end of it, you’ll realize being a slut isn’t very fun, won’t you?”

“I- I- aweady know, dat, daddy. I know. I sowwy. Nevew agains! Nevew agains! Pwease!”

“Hush!” Sam slaps at his ass until the soft pink is brought back up to that wild cherry red. Then he pulls the kitten onto the machine so the dildo is shoved up his hole and turns it on a low setting. “Enjoy, slut.”

 

\-----

 

The second part of Gabriel’s punishment is seven hours later, after some aftercare, snacks, and a short nap. Sam waits until his boy is comfortable and safe and his hole is tightened back up. Then he delivers the final blow. 

“You’re going to fuck yourself on daddy’s cock right now,” he informs him while the boy is half asleep watching his night time cartoons. 

“But-” the boy looks at him with big eyes, shaking his head slightly. “It sowe, daddy.”

“Good. I’m glad it’s sore. Now come fuck yourself.”

With a trembling bottom lip he can’t seem to clamp down on hard enough, he clambors into his daddy’s lap. He tries to steady himself on his daddy’s cock but it hurts the second the big member catches onto his bright red rim. It’s bad enough that his daddy’s cock is already too big for his tiny hole on a usual day, but right now it’s so much worse. It feels like his daddy’s cock grew ten sizes and his tiny hole shrank!

He clutches at his daddy’s shoulders with tiny fingers and cries out as he tries to lower himself further onto the big cock. His little hole tries desperately to flutter and adjust but it’s not working well enough. It’s not adjusting. 

“Oh, daddy. Daddy, pwease,” he sobs and begs, thrashing his head from side to side as he continues to fuck himself downward on his daddy’s big big cock. So big. So so big. 

Sam takes pity on him and starts to kiss the tears away from the corners of his eyes, rubbing circles on his back with one hand while softly cradling the kitten’s cocklet with a finger and thumb, rolling and tugging ever so gently at the abused little kitty part. The small boy in his lap jolts up every few strokes, face bright pink as he gasps and moans, making the prettiest damn sounds for his daddy. 

“That’s it, baby boy. Fuck yourself on daddy. Show daddy how much of a little cock slut his baby boy princess is.” 

“Big big cockswut, daddy. Big wittwe cockswut.” 

“Yes, you are,” Sam says with a nod, sitting back so he can watch his monster cock force itself into his boy’s tiny little hole. He wants so badly to flip them so he can fuck into the boy properly but he knows better. The kitten’s hole is already bright red and puffy and swollen, fighting against him. Anything harder than this and he’ll cause damage. 

Besides, after torturing the kitten all afternoon and night without allowing himself relief even once, he’s pretty damn close to blowing a load inside the little one’s belly. 

With a final shiver, Sam steadies himself and slams the boy home, loving the way he screams himself hoarse when Sam’s massive cock pushes that final bit farther past the puffy little ring of muscles fighting against it. He pumps him full, grinning when the kitten starts to spill milk from his own little cocklet. 

He collapses against Sam’s chest, out of breath and still snotting, sniffling, and crying all over. “I - i- is I aww - aww- aww dones, d- d- daddddddyyy?” he sobs in desperation, needing his punishment to be over. He’s not sure if he’ll survive any more.

“Will you ever let anyone other than daddy touch your little hole or little cock?”

“No! No! Nevew!”

“Will you ever touch anyone else’s little hole or cock?”

“No! Pwomise!”

“Then yes, baby. You’re all done.”

In relief, the kitten clings to him like a little spider monkey, whimpering since his cock is still inside his abused hole, and passes out.

**Author's Note:**

> Stay tuned for their trip to the park!!


End file.
